I don't think any city would be foolish enough to put itself in dire financial straits just to garner corporate investment. Maybe, like many, you don't understand TIFs. They are not give-aways. TIFs are a means by which property is taxed only on its value before development for a set amount of years in order to encourage development. Has it become abused? Of course it has.
I think the reason Amazon didn't choose St. Louis is...who wants to invest in a city where it's front door to the world (downtown St. Louis) has been trashed by corporate investment in favor of a suburb? Ever notice all the construction in downtown Clayton in the past 30 years of so? Centene is about to start their new tower there. The odd thing is all this new construction is mediocre at best, making for a boring skyline. No Helmut Jahns, no I.M. Peis, no Studio Gangs in Clayton (although a Studio Gang 36 story residential tower has been approved at 100 N. Kingshighway,,,and it's a beaut).
Young educated, creative people are far more savvy about urban living and architecture than in the past. When is St. Louis ever gonna realize this?
I think Amazon is seeking a dynamic city that draws top creative talent. Determining what draws such talent isn't any secret, although it seems to have completely eluded the powers that be in St. Louis.
And, by the way, the vast majority of those towers going up and planned in Chicago are condos/appartments...not office buildings. And, I've not been to any large prosperous city that doesn't have rush hour problems.